Studies in Asymmetric Epoxidation of Chalcone Using Quaternary Salts and Nonionic Surfactants Based on 6-Amino-6-deoxy-glucose as Chiral Phase Transfer Catalysts
Quaternary salts and nonionic surfactants based on 6-amino-6-deoxy-glucose were explored as chiral phase transfer catalysts for the asymmetric epoxidation of chalcone. Quaternary salts used in the present study, were void of any branched chain or long hydrocarbon chain, whereas the sugar based nonio...
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Wiley
2011-01-01
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| Series: | E-Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2011/873253 |
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| author | Lalit Sharma Subhash Chander Sharma Saroj |
| author_facet | Lalit Sharma Subhash Chander Sharma Saroj |
| author_sort | Lalit Sharma |
| collection | DOAJ |
| description | Quaternary salts and nonionic surfactants based on 6-amino-6-deoxy-glucose were explored as chiral phase transfer catalysts for the asymmetric epoxidation of chalcone. Quaternary salts used in the present study, were void of any branched chain or long hydrocarbon chain, whereas the sugar based nonionic surfactants have a long hexadecyl moiety as tail. It was observed that quaternary salts showed no activity as phase transfer catalysts but sugar based nonionic surfactants acted as chiral phase transfer catalysts. It was also revealed that hydrophilicity of the surfactant favors more yield whereas stereochemistry governs enantioselectivity. (6,6'-Hexadecylimino) bis(6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose) was found to be the most suitable chiral phase transfer catalyst, resulting asymmetric epoxidation of chalcone with 90% yield and 16.5% enantiomeric excess (ee). |
| format | Article |
| id | doaj-art-abacc35291074e2190003e25f6b31a7a |
| institution | Kabale University |
| issn | 0973-4945 2090-9810 |
| language | English |
| publishDate | 2011-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | E-Journal of Chemistry |
| spelling | doaj-art-abacc35291074e2190003e25f6b31a7a2025-02-03T05:47:04ZengWileyE-Journal of Chemistry0973-49452090-98102011-01-01831293129710.1155/2011/873253Studies in Asymmetric Epoxidation of Chalcone Using Quaternary Salts and Nonionic Surfactants Based on 6-Amino-6-deoxy-glucose as Chiral Phase Transfer CatalystsLalit Sharma0Subhash Chander Sharma1Saroj2Department of Applied Chemistry, Shaheed Bhagat Singh College of Engg and Tech Ferozepur-152 004, IndiaDepartment of Applied Chemistry, Shaheed Bhagat Singh College of Engg and Tech Ferozepur-152 004, IndiaDepartment of Applied Chemistry, Shaheed Bhagat Singh College of Engg and Tech Ferozepur-152 004, IndiaQuaternary salts and nonionic surfactants based on 6-amino-6-deoxy-glucose were explored as chiral phase transfer catalysts for the asymmetric epoxidation of chalcone. Quaternary salts used in the present study, were void of any branched chain or long hydrocarbon chain, whereas the sugar based nonionic surfactants have a long hexadecyl moiety as tail. It was observed that quaternary salts showed no activity as phase transfer catalysts but sugar based nonionic surfactants acted as chiral phase transfer catalysts. It was also revealed that hydrophilicity of the surfactant favors more yield whereas stereochemistry governs enantioselectivity. (6,6'-Hexadecylimino) bis(6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose) was found to be the most suitable chiral phase transfer catalyst, resulting asymmetric epoxidation of chalcone with 90% yield and 16.5% enantiomeric excess (ee).http://dx.doi.org/10.1155/2011/873253 |
| spellingShingle | Lalit Sharma Subhash Chander Sharma Saroj Studies in Asymmetric Epoxidation of Chalcone Using Quaternary Salts and Nonionic Surfactants Based on 6-Amino-6-deoxy-glucose as Chiral Phase Transfer Catalysts E-Journal of Chemistry |
| title | Studies in Asymmetric Epoxidation of Chalcone Using Quaternary Salts and Nonionic Surfactants Based on 6-Amino-6-deoxy-glucose as Chiral Phase Transfer Catalysts |
| title_full | Studies in Asymmetric Epoxidation of Chalcone Using Quaternary Salts and Nonionic Surfactants Based on 6-Amino-6-deoxy-glucose as Chiral Phase Transfer Catalysts |
| title_fullStr | Studies in Asymmetric Epoxidation of Chalcone Using Quaternary Salts and Nonionic Surfactants Based on 6-Amino-6-deoxy-glucose as Chiral Phase Transfer Catalysts |
| title_full_unstemmed | Studies in Asymmetric Epoxidation of Chalcone Using Quaternary Salts and Nonionic Surfactants Based on 6-Amino-6-deoxy-glucose as Chiral Phase Transfer Catalysts |
| title_short | Studies in Asymmetric Epoxidation of Chalcone Using Quaternary Salts and Nonionic Surfactants Based on 6-Amino-6-deoxy-glucose as Chiral Phase Transfer Catalysts |
| title_sort | studies in asymmetric epoxidation of chalcone using quaternary salts and nonionic surfactants based on 6 amino 6 deoxy glucose as chiral phase transfer catalysts |
| url | http://dx.doi.org/10.1155/2011/873253 |
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